A general synthetic route towards gamma- and delta-lactones. Total asymmetric synthesis of (-)-muricatacin and the mosquito oviposition pheromone (5R,6S)-6-acetoxy-hexadecanolide.

Authors
Couladouros, EA Mihou, AP
Citation
Ea. Couladouros et Ap. Mihou, A general synthetic route towards gamma- and delta-lactones. Total asymmetric synthesis of (-)-muricatacin and the mosquito oviposition pheromone (5R,6S)-6-acetoxy-hexadecanolide., TETRAHEDR L, 40(26), 1999, pp. 4861-4862
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
26
Year of publication
1999
Pages
4861 - 4862
Database
ISI
SICI code
0040-4039(19990625)40:26<4861:AGSRTG>2.0.ZU;2-M
Abstract
Five (or six) membered asymmetric lactones are synthesized from gamma-butyr olactone (or delta-valerolactone) in a straightforward way using the follow ing reaction sequence: reduction, Wittig-Schlosser coupling, Sharpless asym metric dihydroxylation, oxidation and lactonization. Thus, (-)-muricatacin is synthesized in six steps (43 % overall yield). Furthermore, (5R,6S)-6-ac etoxy-hexadecanolide is prepared in eight steps (38 % overall yield) via a carbonate ester, utilizing a novel lactonization with inversion of stereoch emistry. (C) 1999 Elsevier Science Ltd. All rights reserved.